I’ve been dating a very nice guy, Tom (not his real name). Tom is widowed, 48 years old, and has a good job as an actuary. I’m single, never married, 36 years old, and have a good job as a corporate trainer.

We dated for about 8 months and things went very well. The only hitch in the whole situation was his son, Nick (not his real name). Nick is 26 years old and lives at home, rent free. He has no job and asks his dad for $50 – $100 every 2-3 days so he can go out drinking with friends, buy something he wants, go to the movies, etc… Nick has a BA in Accounting but has failed the CPA exam twice.

So Tom pays for Nick’s car, Tom pays for Nick’s insurance (health & auto), Tom is paying off Nick’s credit cards that Nick maxed out after college when he couldn’t find a job, Tom pays all the household bills, Tom buys the food, etc… Nick spends all day “Studying” to take the CPA exam again, which he has put off for over a year now. I put the studying in quotation marks because in the 8 months I’ve known him Nick has never said anything about what he read or taking a practice test, or anything that made it sound like he was studying at all. Tom is the one who keeps insisting that Nick is hard at work studying so he’ll ace the CPA exam next time.

Nick is so busy “Studying” that he can’t possibly wash the dishes, mow the lawn, cook a meal, vacuum a carpet, do a load of laundry, etc… Tom blames Nick’s aversion to housework on the fact that Nick’s mom died when Nick was 13. His mom never got the chance to teach Nick how to do those things. Tom was so busy working after her death that Tom hired a housekeeper while Nick was in Middle School and High School.

While his mom’s death is tragic, I don’t understand why that makes a 26 year old man incapable of learning how to pick up after himself now. If he was really lost over how to wash a dish or do a load of laundry, I’m pretty sure he could find a Youtube video to give him a tutorial.

Also, he survived 4 years away at college in another state. So his laundry got cleaned and he fed himself somehow in those 4 years.

Tom spent his entire life putting away money so he could retire at 50. He’s 48 now and has run through a lot of his savings supporting his adult, college educated, son who refuses to get a job that isn’t “worthy” of him. At dinner one night Nick actually said, “If it’s not paying at least $50,000.00 a year, I don’t want it. I know what I’m worth.” Nick blames his dad’s generation for ruining the economy, ruining the job market, and being the reason why Nick can’t find a decent paying job.

This whole thing is between Tom and Nick really isn’t any of my business. Tom is welcome to spend his money as he sees fit. Tom is welcome to cater to his adult son as he sees fit. While we were dating, I kept my mouth shut about all of it. When Tom would complain about how quickly his savings were disappearing, I’d tell him that he should talk to Nick.

Then the “incident” happened. Tom and I were having a quiet night at his place. It was after dinner, and we hanging out on the sofa watching stuff on Netflix. Tom left the room to use the restroom and Nick came home from where ever he’d been. Nick said, “Oh good, I wanted to talk to you alone. Dad’s birthday is in 2 weeks. And it doesn’t seem right to borrow money from him to buy him a gift. So could you give me $100?”

I was shocked. I think I sat in silence for about 5 or 10 seconds before I said, “I’m sorry. I can’t.” Nick said, “That’s ok. I know how hard things can me. Believe me.” And laughed. And then he said, “If you can only give me $50, that would be ok.” Again, I said, “I’m sorry. I can’t.” Nick got a little huffy and said, “Fine, whatever!” and stomped off to his room. When Tom came back, I told him what happened. And then Tom got mad. He couldn’t believe I wouldn’t give Nick the $100. Tom said, “I’ll give you the $100, and you go give it to Nick. I don’t want him to be embarrassed that he can’t buy me a birthday present.” And I said something along the lines of, “That’s ridiculous. Why don’t you just give him the $100 in that case? I don’t want him to think I’m willing to lend money to him. He doesn’t have a job and has no way to pay me back. So basically I’d be giving Nick money and then you’d be paying me back. I don’t want to be in the middle like that.”

Tom got really angry accusing me of calling his son dishonest (because I said Nick wouldn’t pay me back) and lazy (because I mentioned that Nick doesn’t have a job). I told him that his relationship with his son was his business. But my relationship was with him and not his son.

Tom broke up with me. Because, of course, his son is the most important person in his life and if we got married then I’d be Nick’s step mom. It boiled down to, if I was unwilling to have a relationship with Nick, then my relationship with Tom was over.

It’s been a month. Tom and I haven’t talked since that night. I really like Tom. I miss him and I hate that we broke up over this.

Was I out of line? Should I have just given Nick the $100 to buy Tom’s birthday present? Should I have accepted being in the middle to save Nick’s pride? Even if Nick is 26, should I have been trying to build some sort of maternal relationship with him?

I feel like I set the correct boundaries. But maybe I’m just being heartless because I feel that Nick is taking advantage of the situation. And that has colored my actions in regards to lending Nick money.

What do you say, e-Hell? Should I be roasting in the fires on this one? 0829-16

AAAARRGGH! No! No, no, no! You do NOT belong skewered over an EHell bonfire! You are the only normal, healthy, sensible person in this entire scenario. You are questioning your principles and core convictions when you know, deep in your gut, that you are right.

Nick has a serious character flaw which has been nurtured and facilitated by his equally flawed father. It is a PROFOUND unkindness to raise children who are this dysfunctional as adults. Tom has seriously handicapped his son so that he is not able to be a healthy adult who is productive, independent, grateful, hard working and self sustaining. Had you continued in this relationship playing this money game, you would have been complicit in Tom’s miserable parenting and the continued “helplessness” of Nick. Married couples fight about sex, money and the kids and I guarantee that you and Tom, had you married, would have fought vigorously about the kid and how money has been spent. Once married, your finances will combine and you would have fought over how Tom is draining *your* financial reserves supporting an indigent, lazy, ungrateful, wretch of a son Tom helped create.

Run and don’t look back. If Tom calls, do not answer the phone. Wait for a good man to come into your life.

Yikes! Be glad you got out when you did! Even if it wasn’t your choice. Just think about it, if you and Tom got serious, got married, Nick would be still running the show. Go on a vacation? I don’t think so, not unless you include Nick. Have a baby? Are you kidding? That baby would just be taking away the silver spoon from Nick’s mouth, etc….

You get the picture. Nick will ALWAYS come between Tom and whomever he is dating, because Tom allows it . It would be interesting to see what happens in 2 years when Tom cannot afford to retire as he will still be supporting Nick and won’t be able to afford to retire. Even worse, when Tom is 65 and still cannot retire because, the way this story seems to be going, he might be supporting not only Nick but Nick and Nick’s wife or girlfriend and who knows how many children.

I’m sure that Tom sounds like a nice guy, but his relationship with his son sounds like it would cause nothing but friction between you and Tom.

My most charitable assessment of Nick is that he was pushed into a field that he never wanted to be in to begin with, gave up at the very first sign of trouble, and now doesn’t know what to do with himself. Doesn’t excuse him being a sponge, though. Tom needs to get real with Nick. Tell Nick that it’s time to either re-sit the exam or move on, that Nick needs to start paying rent, that he won’t give him going-out money anymore. As everyone else has said, Tom is doing Nick no favors in the long run.

OP, as much as it hurts to let go of a nice guy, it’s probably for the best. If you’re getting hit up for money eight months in, what would happen at the two-year mark? What if you wanted to take your relationship to the next level at some point and combine households? Tom’s got blinders on when it comes to Nick. He broke up with you because deep down, he knows the things he accused you of saying are true: Nick is lazy, and he hasn’t shown himself to be terribly trustworthy, either. If Tom doesn’t wake up, he’d better prepare to fight with every girlfriend he ever has over his son. Don’t let it be you. Do your best to move on, and every time you’re tempted to call Tom, imagine listening to one of Nick’s entitled tirades, fielding requests for money every time Tom leaves the room, looking at the mess Nick’s made of Tom’s home every time you’re over, etc.

Oh dear mother of pearl! I am picking my jaw off the floor. Nick is a lazy bum and Tom is an enabler. Thank your lucky stars you are out of that relationship. And a job with at least 50K starting pay? In his *expletives* dreams.